Anthracycline antibiotics (daunorubicin, adriamycin, Aclacinomycin A, etc.) are of demonstrated utility in cancer chemotherapy. In the past two years we have developed a covergent synthetic approach to 4-demethoxydaunomycinone which should be applicable to a range of aglycone analogs of the rhodomycinone class. We propose to develop and extend this chemistry to produce gram quantities of fully functionalized rhodomycinone aglycones of the natural absolute configuration for coupling with daunosamine and fraudulent sugars. Our approach to aglycones of the aklavinone and citromycinone classes of anthracyclinones is a major new aspect of the proposed work. Several major chemical problems in this area will be explored. First, an efficient synthesis of benzocyclobutendione monoketals--the CD-ring segment of the aglycones in our route--will be explored. This will involve exploring new chemistry to synthesize these systems efficiently. Preliminary studies using silylated benzocyclobutenones have been especially encouraging. A second problem is the development of chemistry for obtaining an AB-ring portion of the aglycone of correct absolute configuration. The third major objective is the convergent synthesis of aklavinone and 11-deoxyrhodomycinone systems employing novel aspects of the chemistry of quinone monoketals. Finally, preliminary work will be investigated towards the synthesis of C-nucleoside-type derivatives of anthracyclinones.